Draft. Some details unconfirmed. Unit counts are Tim's verbal numbers from the calls, not a roster. The Airbnb house-rules deadline (Nov 20 vs end of February) is unverified. The exact date Tim notifies Wheelhouse is his call and has not been set. Confirm all three at kickoff.
Internal RM Brief
Casago Alaska Retreats
Tim Bottomley, Foundertim@casagoalaska.com~70 units · Girdwood + Anchorage · Start Nov 5 · Audit review ~Nov 17
Situation
Tim Bottomley bought Vacasa's Alaska book, closed March 31, 2026, and went live as a Casago franchise on July 1, straight into peak season. He is an account-management and sales leader (Indeed, ZipRecruiter), four months into short-term rentals, based in New Hampshire, and in Alaska every couple of months. He will tell you himself that he does not know everything yet. He does know what good partnership looks like, and he has not been getting it.
At launch he kept Wheelhouse because Wheelhouse had been pricing the territory for Vacasa and it was the continuity choice. Since July 1 he has had three meetings with their revenue manager, a pricing exercise he asked for on all 70 units sat unanswered for over a week, and the calendar reads static to him going into the holidays, ski season, and a summer 2027 that is already booking. He is keeping the Wheelhouse software and moving the service to us. You will work in Wheelhouse and Guesty every day.
His whole 2026 is "stabilize, don't lose owners, then add." Owners are already calling to say reservations are down, and some still carry Vacasa-era frustration. He shortlisted two other RM providers and chose Pacer on attention, depth in the PMS, and two Casago peer references. Once rev ops is stable he wants to add inventory in Wasilla and Palmer this winter. A clean first 90 days opens a bigger book.
Two of Tim's three team members were on both calls. Jammie Trotter is the General Manager on the ground in Alaska (ex-Vacasa, housekeeper to GM) and takes owner calls. Sawyer Beddoes is Director of Operations, based in Medford, OR, and owns listings, OTA logins, and the Airbnb compliance work. Tim makes the decisions.
About 70 live in Guesty, 62 or 63 on Airbnb (7 or 8 units were removed from Airbnb under Vacasa before Tim took over), about 37 homes on Marriott Homes & Villas, and 6 or 7 multi-unit or condo-stack style units. Some inventory is older 1970s condos. These are Tim's verbal counts. Pull the real roster from Guesty in week one.
What's Broken
The OTA relaunch never happened as a relaunch. Only the Airbnb account transferred from Vacasa. Vrbo, Booking.com, Marriott, and Expedia are net-new accounts with zero review history, and nobody enrolled the new listings in promotions or marked up to offset new-listing discounts. Tim has been doing it by hand, three units at a time, late at night. He calls this "the biggest miss." Ranking and conversion on those channels start from scratch, and the audit has to say so before anyone judges Q1 against Vacasa-era channel history.
Channel mix is narrow and the high-ADR channel is bleeding. Vrbo is number one and Airbnb a close second, together 73 to 74% of reservations. Booking.com is a distant third but growing. Expedia was never on under Vacasa, Tim added it, and it is pulling few and poor reviews. Marriott revenue is "a lot" lower than last year across 37 homes. Vacasa.com demand disappeared, and some of what remains is mislabeled as direct in Guesty. There are no true direct bookings yet; Guesty is building their direct site 1.0.
Pace. Tim's own read is about 1.3% behind the comparison period for July 1 through October 28. Whether that is revenue or reservation count, and against what, is unclear. Treat it as his number until Key Data is live. Summer 2027 bookings are already arriving and he thinks they are underpriced on some weekends.
Inherited constraints. Eight units off Airbnb for reasons he inherited. Airbnb review scores he inherited. Owner pricing expectations he inherited, including an owner who wants $150 a night in the off-season and gets nothing. He wants data and talking points to re-educate owners, not a defense of their numbers.
Data integrity. Vacasa-to-Casago transfers at other franchisees loaded booked-on dates incorrectly. Check the Guesty reservation export for the same problem in week one, before anything built on booking date (pace, lead time, channel ADR) goes in front of Tim.
Tools & Systems
PMS: Guesty. This is where the work lives: fees, LOS discounts, cancellation policies, channel markups, listing content. Tim's complaint about his current RM was that they never lived in Guesty.
Pricing: Wheelhouse software stays. Tim likes the product ("plug in Claude and ask questions"). We are added as users and run it. Do not change pricing or min stays in Wheelhouse until Tim has notified Wheelhouse, which he plans to do after CasaCon. Until then, audit only. Our logins will be visible to Wheelhouse inside the software, and Wheelhouse is a Pacer partner, so no negative commentary about them anywhere.
Reporting: Key Data Pro, being set up. Tim had not heard of Key Data before the discovery call and the live demo was a big part of why he signed. Pacer Portal access for Tim, Sawyer, and Jammie, with scoped permissions (see below).
Also in the stack: a cancellation-insurance product adding roughly an 8% fee layer that Tim is testing and that he says changes his pricing philosophy. Reva for review aggregation (just signed, he is committed to it, do not pitch our reviews tab as a replacement). Breezeway for ops. About 25 Google Sheets he would love to retire.
OTA logins and 2FA. Today Tim and Sawyer share a Google Doc and relay codes by text. Marriott is the worst, Booking.com lets us use our own phone number, Airbnb rarely re-prompts. Save everything through the portal credential vault on day one and warn them the first two weeks will be heavy on codes. Nothing in the audit moves until Guesty, Wheelhouse, and the four OTA extranets are open to us.
What We Committed
A dedicated RM in Wheelhouse and Guesty daily, with Shaugnessy leading onboarding and Justin overseeing.
A two-week onboarding audit: every listing (headline, photo order, bad photos, copy, captions) plus a revenue strategy audit on Girdwood and Anchorage history (trends, misses, forward pace YoY and vs market, fee-to-rent ratios, channel mix, lead time, ADR by channel, cancellation policy). Findings presented for Tim's approval. His words were repeated back to him: "you are in charge."
Sequencing agreed on the Nov 3 call: stealth phase this week into CasaCon (access, portal, reservation data, Key Data, Guesty touch-ups), no Wheelhouse pricing changes, then an audit review meeting around Monday Nov 17 while Tim is in Alaska, then we take over pricing and min stays.
Captions rewritten and pushed through the Guesty API. Expedia multi-unit listing setup reviewed for the 6 or 7 eligible units. Booking.com optimized for Alaska's international demand (India, Asia, Europe). A crawlability check on the Guesty direct site once it exists.
Permissioned portal access. Sawyer does not want the whole team seeing company valuation. Tim gets full access; Sawyer and Jammie get scoped access.
Bi-weekly meetings during ramp, tapering to monthly after a full shoulder and peak.
Owner talking points and performance narratives on request. Tim and Jammie hold the owner conversations; we arm them with data. Pacer does not contact owners.
Tim's Style
Candid and talkative. He said "I feel like I've done all the talking" and meant it. Casual, a little profane, warm. He bonded with Shaugnessy over her Alaska ties on the first call.
Thinks in dynamic pricing from ad-bidding. His mental model is Indeed and ZipRecruiter bid calendars. Frame holiday, ski-season, and event pricing that way and he gets it instantly. He still over-indexes on the nightly rate; fees, LOS, cancellation policy, and merchandising are new levers to him. Teach them in the audit.
Economically minded. He ran the numbers on his own options and knows his thresholds. Bring numbers, not adjectives.
Owner retention is the scoreboard. He is "the new owner of the management company in town" and every owner call is a trust test. Anything that helps him look competent to an owner is a win.
Expects responsiveness. His single biggest complaint about the incumbent was silence between monthly meetings. Over-communicate for the first 90 days.
Protective of people. He would not blame his current Wheelhouse rep (on honeymoon) and he does not want anyone bashed. Match that.
Week 1 Priorities
Access: Guesty user, Wheelhouse user, Airbnb, Vrbo, Booking.com, Expedia, Marriott extranets, saved to the portal vault. This gates everything.
Pull the full Guesty reservation export and validate booked-on dates against Vacasa-era reservations before building any pace or lead-time view.
Build the live roster: 70 in Guesty, which 7 or 8 are off Airbnb and why, which 37 are on Marriott, which 6 or 7 qualify as multi-unit for Expedia.
Listing audit on all ~70: headlines, photo order, captions, amenities, promotions, new-listing markup status on Vrbo, Booking.com, Expedia, and Marriott.
Revenue strategy audit on Girdwood first (50+ units, ski season starting): forward pace for holidays and ski season, summer 2027 on-the-books ADR vs last year, fee and LOS settings in Guesty, channel ADR and lead time. Anchorage second.
Read-only in Wheelhouse. Document the current strategy, min stays, and owner constraints so the takeover after Nov 17 is a reset, not a scramble.
Kickoff Call Agenda
Wheelhouse timing: confirm the exact day Tim notifies Wheelhouse. Nothing changes in Wheelhouse before that day, and the audit review follows it.
Roster: confirm unit count, the 8 off Airbnb, and any units Tim wants excluded.
Airbnb house rules: Sawyer heard Nov 20, Shaugnessy recalled end of February. Confirm the real deadline and have Sawyer proceed either way; we take the headline and copy pass separately.
Portal permissions: what Sawyer and Jammie should and should not see. Valuation stays with Tim.
Owner cadence: when Tim and Jammie have owner calls, what format of talking points they want, and how far ahead they need them.
Meeting rhythm: lock the bi-weekly slot and who attends from their side.
Transition Context
Do not touch pricing or minimum stays in Wheelhouse until Tim has notified Wheelhouse. He is deliberately keeping their service running through CasaCon so there is no dead period, and he does not want them surprised by a reset. Audit, document, and prepare. The handoff is after the Nov 17 review.
Before Nov 17: you are inside Guesty and the OTAs with full authority to fix listings, promotions, markups, fees, and settings. Wheelhouse is read-only. This is the audit and trust-building phase, and most of the channel damage can be repaired here without touching a nightly rate.
After Nov 17: you own the calendar in Wheelhouse, min stays, and the full stack. Tim will be in Alaska that week and wants to talk strategy while he is in-market. The first things he will look at are the holiday and ski-season calendar and the summer 2027 on-the-books ADR.
Set the channel expectation in the audit. Four of five OTA accounts started from zero reviews in July. If you do not frame that, Q1 results on Vrbo, Booking.com, Marriott, and Expedia will be judged against a Vacasa-era history that no longer exists.